Morpholino Analogues of Fingolimod as Novel and Selective S1P1 Ligands with In Vivo Efficacy in a Mouse Model of Experimental Antigen-Induced Encephalomyelitis

Int J Mol Sci. 2020 Sep 4;21(18):6463. doi: 10.3390/ijms21186463.

Abstract

Multiple sclerosis (MS) is a chronic, inflammatory, autoimmune disease of the central nervous system (CNS) which is associated with lower life expectancy and disability. The experimental antigen-induced encephalomyelitis (EAE) in mice is a useful animal model of MS, which allows exploring the etiopathogenetic mechanisms and testing novel potential therapeutic drugs. A new therapeutic paradigm for the treatment of MS was introduced in 2010 through the sphingosine 1-phosphate (S1P) analogue fingolimod (FTY720, Gilenya®), which acts as a functional S1P1 antagonist on T lymphocytes to deplete these cells from the blood. In this study, we synthesized two novel structures, ST-1893 and ST-1894, which are derived from fingolimod and chemically feature a morpholine ring in the polar head group. These compounds showed a selective S1P1 activation profile and a sustained S1P1 internalization in cultures of S1P1-overexpressing Chinese hamster ovary (CHO)-K1 cells, consistent with a functional antagonism. In vivo, both compounds induced a profound lymphopenia in mice. Finally, these substances showed efficacy in the EAE model, where they reduced clinical symptoms of the disease, and, on the molecular level, they reduced the T-cell infiltration and several inflammatory mediators in the brain and spinal cord. In summary, these data suggest that S1P1-selective compounds may have an advantage over fingolimod and siponimod, not only in MS but also in other autoimmune diseases.

Keywords: ST-1893; ST-1894; experimental antigen-induced encephalomyelitis; immunomodulator; lymphopenia; morpholino analogues of fingolimod; multiple sclerosis; sphingosine 1-phosphate.

MeSH terms

  • Animals
  • CHO Cells
  • Central Nervous System / drug effects
  • Cricetulus
  • Disease Models, Animal
  • Encephalomyelitis / drug therapy
  • Encephalomyelitis, Autoimmune, Experimental / drug therapy
  • Encephalomyelitis, Autoimmune, Experimental / metabolism*
  • Fingolimod Hydrochloride / analogs & derivatives
  • Fingolimod Hydrochloride / pharmacology*
  • Immunosuppressive Agents / therapeutic use
  • Ligands
  • Lymphopenia / drug therapy
  • Lysophospholipids / metabolism
  • Mice
  • Morpholinos / pharmacology*
  • Multiple Sclerosis / drug therapy
  • Multiple Sclerosis / metabolism
  • Receptors, Lysosphingolipid / metabolism
  • Sphingosine / analogs & derivatives
  • Sphingosine / metabolism
  • Sphingosine-1-Phosphate Receptors / drug effects
  • Sphingosine-1-Phosphate Receptors / metabolism
  • Spinal Cord / drug effects
  • T-Lymphocytes / drug effects

Substances

  • Immunosuppressive Agents
  • Ligands
  • Lysophospholipids
  • Morpholinos
  • Receptors, Lysosphingolipid
  • Sphingosine-1-Phosphate Receptors
  • sphingosine 1-phosphate
  • Fingolimod Hydrochloride
  • Sphingosine